Managing an Employee Who Wants to Impress You All the Time

Executive Summary

Every leader knows they shouldn’t play favorites but there will always be team members who want to make it into your inner circle. If a direct report is singularly focused on pleasing you, it’s your job to refocus them. Here’s how. Avoid feeding their need to please. Because of your power and their fear, you may have to watch yourself more carefully than you do with other subordinates. Give the person the same amount of time and attention you do other employees. And make sure you hold them to the same standards of performance. If they spend too much time checking in and gauging your reactions, guide them to make their own decisions. Assign them to work with other leaders or project teams. This will take the pressure off the unhealthy dynamic between you and increase the chances that they collaborate better with others.

Every leader knows they shouldn’t play favorites — it can lead to dissatisfaction and discord on a team. There are even some surprising disadvantages for the person who is the focus of the boss’s special attention. But there will always be team members who want to make it into your inner circle, and sometimes a subordinate can be singularly focused on pleasing you and gaining your favor.

This kind of courtship usually comes from fear, and is often a misguided attempt to protect their self-image and their job status. Unfortunately, while they’re obsessing over keeping you happy and tending to nonessential tasks that they hope will reinforce their relationship with you, they may be neglecting their real work and creating friction with their peers. Here are four ways you can redirect this attention back to their performance.

Avoid feeding their need to please. Because of your power and their fear, you may have to watch yourself more carefully than you do with other subordinates. I’ve observed relationships in which pleasers were willing to eat, watch (TV and movies), or wear what the boss liked, all in an effort to create a sense of companionship. This kind of sucking up can become dangerous if the boss succumbs to affinity (or similarity) bias and gives the pleaser more attention because of their supposedly shared likes. One of my clients came to enjoy this kind of “tending” by a subordinate several levels down and it was a tough habit to break. It wasn’t until multiple members of her leadership team came to her and expressed their concerns about the subordinate’s influence that she realized that she had gotten sucked in and needed to reestablish a more impartial relationship.

Structure your interactions to balance special attention with objectivity. If you have weekly one-on-ones with your direct reports, make sure everyone gets the same amount of time (even if the pleaser requests more) and be sure you’re giving kind and simultaneously rigorous feedback to everyone. Relying on concrete scheduling and project management tools can be especially important, if you work in an office where people drop in for ad hoc discussions and the person could monopolize your time.

At another client company, a vice president and the CEO both worked on the design side of the business, and spent much of the workday together, brainstorming and collaborating. The vice president purposefully buttered up the CEO to gain special privileges and to deflect attention from the fact that she sometimes didn’t meet project deadlines or budgets. The CEO enjoyed the VP’s attention but eventually some of the subordinate’s weaknesses had real costs for the business. The CEO started setting specific dates and times for meetings rather than casually spending most of the workday with her, and also began holding her to milestones and other commitments, expressing dissatisfaction when she missed them. As he continued formalizing and distancing their relationship, she became more stressed, couldn’t deliver on her obligations, and eventually left the firm. As a result, the CEO became more available to other employees, who were able to implement projects more efficiently.

Guide them to develop their own decisions. Ingratiating employees may be overly worried that you’ll be unhappy with them or their work; the thought of disappointing you can become overwhelming for otherwise competent, experienced people. One senior leader I worked with was so concerned about failing to fulfill the CEO’s expectations that she was sometimes afraid to move forward with her own judgments and proposals. The CEO became frustrated with the subordinate’s small tentative steps and constant checking. As an interim solution, I worked with the CEO to be clearer about project requirements and with the subordinate to give the CEO sets of options that included clearly differentiated assumptions. By gauging his reactions to these differing scenarios, she was able to better understand his thought process. Over time, the subordinate developed more confidence in being able to generate proposals the CEO would accept, and the relationship became less fraught for both of them.

Assign them to work with other leaders or project teams. This will take the pressure off the unhealthy dynamic between you and increase the potential for them to collaborate better with others. In fact, research has shown that fawning on the boss can diminish self-control; pleasers may put so much energy into observing and interacting with you that they exhaust their capacity to deal with others, particularly when they’re stressed or frustrated. By explicitly directing their attention away from you, you’ll learn whether they have the capacity to behave better with their colleagues.

The owner of a company I worked with hired a family friend who viewed him as the sole power source. The friend assumed that if he kept the owner happy, he wouldn’t have to bother taking anyone else seriously. When it became clear that the subordinate was flattering and deferential to the boss but high-handed and uncooperative with teammates, the owner agreed to reassign the friend to report to the company president. The president and I developed an action plan to clarify the subordinate’s responsibilities and performance expectations. Even after reducing his scope of work, the requirements for collaboration turned out to be too much pressure, and the subordinate eventually left the company on his own.

It’s better for everyone when subordinates’ competence and performance earn them recognition and regard, rather than special status with the boss. By adopting these four approaches, you’ll have a much better chance of getting your pleasing subordinate on a more independent path that will serve you and the organization.